I am a bochur in the parsha who is facing the following dilemma for many years.

Girls who follow Yeshivish hashkafos are rejecting me simply because I grew up in the Modern velt.

Girls who follow Modox hashkafos (even the ones that are frummer, not like Ivanka Trump) are rejecting me because I became more greasy when I learned in Yeshivas OJ after graduating my co-ed day high school.

The application of these generalities to shidduchim, where we need to consider a single individual is bizarre. I would hope that if one were to seek the advice of a Chochom on this, there would be no such pronouncements. It is tragic that nonsense like this is used to pass judgment on someone who has not been considered for who he or she is.

In our generation, we are privy to the myth of the “learning boy”, or the girl who wants to marry a “learning boy”. This entire concept is a simple lie, and has zero bearing on the individual’s true dedication to Torah or learning, nor the hashkafos of either candidate. Labels are completely artificial, and those with smarts should realize that a shidduch is being proposed for this girl with this boy, which needs to be considered on its own merits.

I live in NY, and I am 23. I started the parsha when I was 21. I have been having the same problem mentioned above ever since.
Shadchanim I’ve met with have not suggested many out of town girls, in spite of the fact I have always been open to dating them.

You are clearly talking to the wrong shadchanim and looking at the wrong girls. There are plenty of girls with hashkofos that aren’t inherently hypocritical like you are describing. Maybe check out people that live in the Hinterlands, AKA that foreign country some people refer to as Not New York Or New Jersey.

The gemora in Bava Kama describes a similar situation. A man had two wives, a young one and an old one. The young one would pull out his white hairs whereas the old one would pull out his black hairs, so he said, I am קרח מכאן and קרח מכאן, bold from either side.

“There are plenty of girls with hashkofos that aren’t inherently hypocritical like you are describing.”

With all due respect to the OP, I don’t see why the hashkafos are “inherently hypocritical.” People want to be with their own kind; I don’t think that’s shallow. If he’s not MO, he should expect to have trouble with MO girls. If he’s not super right-wing (as is evidenced by his willingness to date MO girls) then he should expect to have trouble with super right-wingers. If he’s a centrist, then there are plenty of people out there like that and I’m not sure why he’s not being set up with them.

Well my parents and everyone says you cannot just say “I’d be okay with x, y, and z” because that’s an invitation to go doulbley far on such a road. In a shidduch world where everyone tries to conceal information “shy” can mean basically socially awkward to autistic and “openmindness” can equal openness in hashkafa.

You need to see different people and be super clear where you are holding. Don’t say “I’d date former MO girls” say “I want to date someone with my hashkafos, I don’t really mind where she comes from as long as were holding together in the same place now”.

I’m a former OOT girl. I live in-town now but I’m an OOT at heart, I feel like it’s hard to find someone who gets the mentality of OOT.

If my values are 100% identical to the Yeshivish velt, then why should the other parties raise an eyebrow over the co-ed mosdos I went to when I was younger?
If My yeshiva in E”Y had and my limud hatoireh כיום have much stronger impact on my values than the Hollywood propaganda I grew up watching on my parents’ television, then why would a standard Bais Yaacov girl say no to me? And are these types of girls at greater risk of having Shalom Bayis issues if their husbands grew up MO????

Careful. Don’t get in over your head with the capabilities of the Rebbe and Mashgiach from an anonymous yeshiva. We may have no clue who that individual is, and even less knowledge of how much they grasp outside of the gemora. Not every Rebbe or Rosh Yeshiva is able to advise on these matters, as long as they are aware of their limits. This is not a put down at all, just a statement how careful we must be when seeking or offering advice. I have been asked for advice on the stock market. I reject the request, as my understanding of it is extremely poor, while I do have advanced knowledge and training in other areas.

A more general comment – Oh the labeling. We fall into the trap of these labels about someone’s hashkafos, as if they have any bearing at all on fact. Personally, I have found these broad generalizations highly misleading, aside from being poorly understood in the first place.